Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes

Naoya Ohmura, Asami Nakamura, Akiyuki Hamasaki, Makoto Tokunaga

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed.

Original languageEnglish
Pages (from-to)5042-5045
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - Oct 1 2008

Fingerprint

Amides
amides
Lactams
catalysts
Propane
Catalysts
Isomerization
propane
isomerization
hydrolysis
Hydrolysis

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes. / Ohmura, Naoya; Nakamura, Asami; Hamasaki, Akiyuki; Tokunaga, Makoto.

In: European Journal of Organic Chemistry, No. 30, 01.10.2008, p. 5042-5045.

Research output: Contribution to journalArticle

Ohmura, Naoya ; Nakamura, Asami ; Hamasaki, Akiyuki ; Tokunaga, Makoto. / Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes. In: European Journal of Organic Chemistry. 2008 ; No. 30. pp. 5042-5045.
@article{801af926da3a4d7e8e7c782e02ce6895,
title = "Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes",
abstract = "Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed.",
author = "Naoya Ohmura and Asami Nakamura and Akiyuki Hamasaki and Makoto Tokunaga",
year = "2008",
month = "10",
day = "1",
doi = "10.1002/ejoc.200800771",
language = "English",
pages = "5042--5045",
journal = "Liebigs Annalen der Chemie",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "30",

}

TY - JOUR

T1 - Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes

AU - Ohmura, Naoya

AU - Nakamura, Asami

AU - Hamasaki, Akiyuki

AU - Tokunaga, Makoto

PY - 2008/10/1

Y1 - 2008/10/1

N2 - Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed.

AB - Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed.

UR - http://www.scopus.com/inward/record.url?scp=55049126397&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=55049126397&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200800771

DO - 10.1002/ejoc.200800771

M3 - Article

SP - 5042

EP - 5045

JO - Liebigs Annalen der Chemie

JF - Liebigs Annalen der Chemie

SN - 1434-193X

IS - 30

ER -